The Room Podcast

Joining us this week is Kashish Gupta, co-founder and CEO of Hightouch. Hightouch is a software for your data stack that syncs any data warehouse to the SaaS tools that your business runs on, making internal usage and sharing easier for everyone. Kashish talks to us about the current state of the modern data stack community and how the industry is constantly pushing forward. He describes how this plays into their sales tactic of “evangelizing” larger corporations by teaching them about “Reverse ETL” and how Hightouch works without pushing the sale. We cover themes such as starting a company with two of his good friends and the procedures they take when it comes to decision-making, the perfect modern data stack, and how to sell your business when the product is something that no one has heard of yet. For The Room Podcast in your inbox every week, subscribe to our newsletter. 6:00 - Where did Kashish grow up and how did that shape his view of the world?8:08 - Did Kashish always want to be a founder?9:27 - How did Kashish's education impact his professional goals?13:08 - What is the story behind Mama’s Cooking?15:01 - What was the “aha” moment that got Kashish thinking about Hightouch?18:10 - How do businesses take advantage of Hightouch?19:56 - How is Kashish's relationship with his partners, Tejas Manohar and Josh Curl?21:28 - How do Kashish's and his partners split up responsibilities and tasks?22:24 - How do Kashish and his partners handle things when there is a disagreement?25:03 - What part of the go-to-market is Hightouch going to continue investing in?27:58 - Who was the first person to say yes to investing in Hightouch? 29:51 - When is the right time for a company to embrace its data warehouse?32:29 - What is Kashish's stance on the semantic layer?34:38 - What are some tools in the modern data stack?35:39 - What tools does Kashish recommend for a company building their modern data stack?38:15 - What advice would Kashish give to an entrepreneur building in this space?40:44 - What’s next for Kashish and Hightouch?44:00 - Who is a woman that has had a profound impact on Kashish and his career? WX Productions

We have another incredible episode in store with Cynthia Plotch and Jamie Norwood, the founders of Stix, the company transforming women's health experiences. Stix was founded to “create a convenient, discreet, and judgment-free way to get the products you need.” Cynthia and Jamie walk us through their negative personal experiences that drove them to create Stix. Plus, they share their ideas to evolve Stix past being just a DTC brand and becoming an entire community of women who can help each other with anything health related. Cynthia and Jamie also explain what led them to go down the VC route for funding this journey. Themes in this episode include knowing when is the right time to fully commit yourself to your passion project, today’s women’s health climate, and what's next in DTC. For The Room Podcast in your inbox every week, subscribe to our newsletter. 4:30 - What were the first few years of Jamie’s career like?5:17 - What brought Jamie to Hungry Harvest and broke her into the world of D2C?6:18 - How did Cynthia’s early career influence her decision to start Stix?9:35 - Did Cynthia and Jamie always plan on being founders?11:26 - When did Cynthia and Jamie know that they were ready to go full-time on Stix?16:41 - How would Cynthia and Jamie describe Stix?17:52 - What was the initial mission for Stix when Cynthia and Jamie founded it?19:29 - How has Stix been connecting to its community and helping solve their problems?23:30 - What prompted Cynthia and Jamie to raise VC funding?25:39 - What advice would Cynthia and Jamie give to founders thinking about starting in D2C?27:25 - What is the process like of getting an affordable product delivered discreetly to those who need it?29:32 - Why is it so crucial for Stix products to be delivered discreetly?33:16 - What does the future of D2C look like?35:27 - What does Amazon acquiring One Medical mean for the future of health care?37:54 - Who is a woman in Cynthia and Jamie’s lives that has had a profound impact on them and their careers? WX Productions

This week we chat with another phenomenal guest, William Santana Li, the founder and CEO of Knightscope. Knightscope is the developer and manufacturer of autonomous security robots. William explains how and why Knightscope was created and why he believes that the future of national security is autonomous. William details his professional experience in the auto and motor industry and how even that couldn’t prepare him for the unorthodox lifestyle of a founder. In today’s conversation with William, we chat about his unique founding story after being an entrepreneur and executive for 30 years. Plus, we dive into topics such as different ways to get funded, how robots are fighting crime in the U.S., and the future of robotics and technology in public safety. Let’s open the door. For The Room Podcast in your inbox every week, subscribe to our newsletter.4:48 - Did William have an interest in the vehicle and motor space from a young age? 7:51 - How was William’s early experience as a founder starting Knightscope?9:45 - What did William learn during the fundraising process of Knightscope?17:04 - Why is William so passionate about preventing crime and protecting the safety of Americans?22:19 - How was the experience of starting from the ground and creating a legitimate robot?26:10 - How is William staying focused on the blend of hardware and software with Knightscope?28:19 - What advice does William have for a founder with a product that is starting locally but wants to go nationwide?30:27 - When building Knightscope, was there a time when things didn't go as planned? 32:58 - How does William think that robots will change public safety and security?36:55 - What does a Knightscope robot do to report crime and build safety?39:31 - Why is it that William is the only male on the board for Knightscope?45:57 - Who is a woman in William’s life that has had a profound impact on him and his career? WX Productions

Season 7 continues with another incredible episode as we chat with Kelsey Mellard, co-founder and CEO of Sitka. Sitka is an online network of experts in medicine, technology, policy, and product with the goal of making access to specialists more available for all people. Kelsey talks to us about her initial career in healthcare, both public and private, and what that taught her before she began her journey of founding Sitka. Kelsey also details her experience of raising a baby and a company at the same time and how her investors felt when she broke the news. The themes of this episode include; problems in the healthcare system and how Sitka is making a difference, the complexities of being a new mom while founding a company, and lessons learned in developing a core product and go-to-market strategies. For The Room Podcast in your inbox every week, subscribe to our newsletter. 5:04 - How did beginning in the public sector help form Kelsey’s view of the world?6:35 - What has Kelsey learned about the complexities of the healthcare system?8:27 - How did Kelsey’s career drive her to start Sitka?11:00 - Did Kelsey ever think she was going to become a founder? 12:16 - What problem did Kesley identify that encouraged her to create Sitka?13:27 - What were some of the early days like in founding Sitka?15:00 - What product did Sitka take to market?16:42 - What lessons did Kelsey learn during the creation and evolution of Sitka’s core product?18:36 - What was Kelsey’s fundraising journey like?23:45 - What did Kelsey learn when developing her go-to-market strategy?27:24 - What does Kelsey think will become the status quo five years from today that perhaps right now maybe would sound very unlikely?30:47 - What did Kelsey’s investors say when she told them that she was having a baby while running the company?36:49 - What is something that Kelsey is excited about moving forward?38:10 - What should users and potential Sitka users be looking forward to?39:17 - Who is a woman in Kelsey’s life that has had a profound impact on her and her career? WX Productions

Welcome back to The Room Podcast. We kick off Season 7 with Spencer Rascoff, co-founder and previous CEO of Zillow. Spencer walks us through how he and the team came up with the idea for Zillow and the unforgettable “Zestimate” feature. Prior to Zillow, Spencer had been the founder of Hotwire, which sold to Expedia for $685 million. Currently, Spencer is an active angel investor in more than 100 companies and is incubating several more through his startup studio and venture capital firm, 75 & Sunny. He serves as executive chair of dot.LA, a news site covering the Los Angeles tech scene and he is co-founder and board chair of Pacaso, the company pioneering a new way to own a second home. In our conversation today, we explore insights and themes such as the art of a killer feature, like the Zestimate, managing team morale and execution amidst a macroeconomic downturn, and why the future of real estate is fractional. For The Room Podcast in your inbox every week, subscribe to our newsletter. 5:05 - Where did Spencer grow up and how did that change his view of the world?6:33 - Did Spencer always want to be a founder?7:38 - What was the public opinion of the internet when Spencer was at Harvard? 11:23 - What did Spencer learn about being an entrepreneur from his experience at Harvard?13:23 - What was the aha moment that sparked the launch of Zillow?15:51 - How did Spencer and the team hone in on the specific product feature for Zillow?19:04 - Did Big Data play any role in the start of Zillow? What was the data stack at the time?21:15 - Who was the first external investor to say yes to investing in Zillow?21:53 - What is the best case board dynamic?26:04 - How did Spencer balance internal and external stakeholder management through his founding journey?29:52 - What advice would Spencer give to entrepreneurs navigating “the early stages of our recession?”31:49 - What is Spencer hoping to accomplish with Pacaso and “fractional ownership” of property?34:08 - What is the user journey of purchasing a Pacaso home? 35:09 - What is one sector that Spencer believes is undervalued at the moment?35:33 - Who is a woman that has had a profound impact on Spencer and his career? WX Productions

In our final episode of season 6 of The Room Podcast, we close out with another incredible guest, Anvisha Pai, Co-Founder and Chief Product Officer of Dover. Dover is a modernized recruiting platform that adapts to your business's needs to connect you with people that you would want to meet and that would want to meet you. In this episode, we and Anvisha discuss her journey as a multi-time founder growing up in Mumbai as the daughter of two doctors. Plus, Anvisha shares recruiting and hiring advice for start-ups and her thoughts on the future of work and hiring automation. For The Room Podcast in your inbox every week, subscribe to our newsletter. 3:40 - Where did Anvisha grow up and how did that shape her view of the world? 4:50 - Did Anvisha always think she was going to become a founder? 6:35 - How was Anvisha’s training as an engineer helpful from a product perspective?9:33 - How did Anvisha go from Product Manager at Dropbox to a multi-time founder?12:28 - What were Anvisha’s takeaways from her experience at the Y Combinator?14:23 - How does Dover automate the initial candidate sourcing? 18:19 - How was Dover's fundraising journey, how did that experience impact the team and what were some lessons learned along the way?22:05 - How has a content marketing approach contributed to the growth of the customer base for Dover?23:53 - How does Dover think about training data sets without creating a potential bias that can be embedded in the data?25:59 - What positive and negatives come from scaling up from a leadership perspective? 28:40 - What is Anvisha’s perspective on the future of recruiting, given the context of the last two years? 30:21 - What is Anvisha excited about in Dover's near future? 31:55 - What's next for Anvisha?32:55 - Who is a woman in Anvisha’s life that had a profound impact on her and her career? The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley. WX Productions

In this special episode of The Room Podcast, we get to listen LIVE as Madison interviews David Yuan, long-time investor and more recently, Founder and General Partner of Tidemark Capital. Tidemark is a venture capital firm built to serve category-leading technology companies as they succeed and scale. In this episode, Dave details how he went from investor to founder and is now a fund founder with Tidemark. Plus, we discuss focused investment themes, the people and processes needed to build a successful firm, and the future of fund transformation. For The Room Podcast in your inbox every week, subscribe to our newsletter. 9:42 - Live Interview Begins9:54 - Dave Introduction12:25 - How was Dave’s early journey as a founder?14:17 - How important is a founder's resume when selling themselves to investors?16:02 - How does Dave think about pitching investment theses to LPs?18:17 - When starting Tidemark, who did Dave go to for help?19:40 - What is one thing Dave wished he knew starting the 2021 year?23:04 - How does Dave think the LP market will change over the next 5 years?26:21 - Who is a woman in Dave’s life that has had a profound impact on him and his career? The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley. WX Productions

We are joined this week by Andrew Savage, Founder & CEO of Suma Brands, a commerce platform focused on developing marketplace brands, specifically on Amazon. Andrew is using his experience from helping establish early E-Commerce for Target and Amazon to guide other growing retailers to high-level success. Andrew and Suma Brands will “find, acquire, and help brands realize their potential.” In this episode, we chat about what is an “aggregator” in the sense of online retail and Andrew’s quintessential blend of focuses that most companies must adhere to; retail, tech, and content. Plus, Andrew shares his thoughts on the evolution of E-Commerce from its origin to now, and even some of his future predictions. For The Room Podcast in your inbox every week, subscribe to our newsletter. 3:48 - Where did Andrew grow up and how did that shape his view of the world?6:24 - Did Andrew always think he was going to be a founder?7:28 - What was Andrew’s early career path like while focusing on E-Commerce?10:52 - What were some “aha” moments while establishing early E-Commerce for Amazon and Target?13:06 - How has Andrew's experience been, being a part of the Amazon ecosystem?14:48 - What is Suma Brands and when did Andrew realize he wanted to found the company?18:31 - What inspired the name of Suma Brands?18:38 - What does it mean to be an aggregator, and does the term apply to Andrew’s business model for Suma?20:43 - What separates Suma from its competition?23:59 - Who was the first investor of Suma Brands and what was that experience like?26:03 - What things are Suma Brands looking for when considering acquiring a retailer?28:41 - Is Suma Brands focused on retail, tech, or something else?30:46 - What trends is Andrew seeing in the E-Commerce ecosystem that will continue to gain traction over the next few years?32:01 - What’s next for Andrew personally?32:51 - Who is a woman in Andrew’s life that impacted him and his career? The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley. WX Productions

S6E5: Lisa Bubbers, Co-Founder of Studs, is Bringing the Ear-Piercing Industry into the Modern Era with Integrated Piercing and Shopping Experiences Our season continues with Lisa Bubbers, Co-Founder and Chief Brand Officer of Studs, the modern platform for ear-piercing and earrings. Studs is all about safe and accessible ear-piercing for all people. Plus they have an easy-to-use, refreshingly branded e-commerce website with every earring fashion choice available. In this episode, Lisa talks to us about what “Earscaping” means to them, as well as what it’s like building a business with a complementary co-founder and the future of the modern shopping mall. For The Room Podcast in your inbox every week, subscribe to our newsletter. 4:47 - Where did Lisa grow up and how did that shape her view of the world? 5:43 - Did Lisa always think she was going to become a founder? 6:51 - How did Lisa’s degree in Visual Studies from UPenn translate into her early work experience? 8:52 - What lessons did Lisa learn around the intersection of the digital and physical while working at Jonathan Adler and home Polish?11:11 - What does the term “Earscape” mean to Lisa and Studs?14:00 - How did Lisa meet her partner, Anna, and what got them started on the founding journey together?15:27 - What advice would Lisa have for new founders looking for co-founders?16:53 - Who was the first person to say yes to investing in Lisa and Studs?17:48 - What was Lisa’s first piercing experience like?19:07 - How is Studs thinking about the future of omnichannel retail?20:18 - How did the pandemic affect Studs business?21:46 - What is the feeling that a customer gets when walking into a Studs store?23:10 - What does Lisa think the modern mall will look like in five years?25:05 - What are some of the tools in Studs’ D to C tech stack?26:29 - Has Studs considered a subscription model? Why or why not?27:27 - What’s next for Studs?29:09 - What’s next for Lisa?30:18 - Who is a woman in Lisa’s life that has had a profound impact on her and her career? The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley. WX Productions

We are returning this week with another incredible guest, Sarah LaFleur. Sarah came up with the idea to create comfortable and fashionable, professional attire for women because she herself found that whenever she was searching for work outfits, it seemed that fashion would always be sacrificed for comfort. In this episode, we discuss the current state of the apparel market and how things have changed so rapidly due to the evolution of the internet and e-commerce, the future of DTC from the brand and consumer perspectives, and how previous work experiences influence a persons fashion choices. For The Room Podcast in your inbox every week, subscribe to our newsletter. 4:05 - What did Sarah take away from her college career, especially at Harvard?8:17 - What was the fashion industry like at that time of Sarah’s early career? 12:24 - What was the aha moment when Sarah knew that she wanted to become a founder?17:52 - What were some of the early supply chain processes of iterating and designing some of the first garments that were built for the “modern American woman?”23:07 - What advice would Sarah give to founders who are looking to raise today in retail and e-commerce spaces?23:34 - What advice would Sarah have to any founder today who might be thinking they’re going to disrupt retail?27:04 - What does Sarah think the future of selling directly to the consumer is?29:00 - Should women seeking to be mothers be freezing their eggs?33:33 - Who is a woman in Sarah’s life that has had a profound impact on her and her career? The Room Podcast is sponsored by our friends at Silicon Valley Bank and Cooley. WX Productions